Synthesis of a rotaxane Cu(I) triazolide under aqueous conditions

J Am Chem Soc. 2013 Sep 11;135(36):13318-21. doi: 10.1021/ja407446c. Epub 2013 Aug 28.

Abstract

We describe the serendipitous isolation of a stable, neutral, monomeric mechanically interlocked Cu(I) triazolide under aqueous conditions. This "trapped" intermediate of the CuAAC catalytic cycle is sterically protected from reprotonation by the rotaxane architecture, which renders the Cu(I)-C bond stable toward moisture and air--even carboxylic acids protonate the Cu(I)-C bond only slowly. The isolation of this remarkably stable Cu(I) organometallic points toward potential applications of mechanical bonding in the study of reactive intermediates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Copper / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Rotaxanes / chemistry*
  • Triazoles / chemistry*
  • Water / chemistry

Substances

  • Organometallic Compounds
  • Rotaxanes
  • Triazoles
  • Water
  • Copper